Maxwell hit the landmark milestone in last week’s Scottish Junior Cup tie at Glentanar, and he has never hidden what the club means to him.
The bulk of his tenure has been spent with the club in exile in Cumbernauld after they left Adamslie Park at the end of his first season in 2014.
Despite the challenging circumstances, Maxwell guided Rabs to their first cup win in 43 years when they beat Shettleston to win the Sectional League Cup in 2016.
There have been memorable Scottish Junior Cup and West of Scotland Cup runs, notably beating Auchinleck Talbot 4-3 on their own pitch in the 2019 West semi-final, only to lose to Beith on penalties in the final.
And in 2017 they took the West Super League title race all the way to the wire, finishing second just three points behind Glenafton.
Maxwell admitted that his love of Rob Roy has kept him at the club when others might have walked away.
He said: “One of the committee said recently it's been the toughest period in Rob Roy's history, but I’ve stuck with it. I don’t know whether other guys would have.
"People have asked whether my loyalty is overriding my ambition but I genuinely do love the club.
"Whenever it ends, and hopefully it’s at a good point and the club gets back home, forget about me – at some point I’d like to think I’ve left a good legacy of what I’ve done at Rob Roy.
"There’s been a lot of unbelievable games we’ve been involved in. Obviously the highlight for any manager is winning a trophy and a lot of good managers don’t get that chance.
"To get into the winners’ circle as a manager, it felt better than when I played and won things. I never thought it would feel like that.
"To lift the first cup in close to 50 years meant a lot.
"But I’m a big believer that Rob Roy will never get the luck they deserve until the infrastructure is sorted. Things will always be fractured, and come the end of this season if we manage to stay in this league, that will be the biggest achievement ever. To keep this team in this league will be unbelievable."